(1R,4S,5S)-4-((S)-1,2-bis(benzyloxy)ethyl)-5-fluorocyclopent-2-enyl methyl carbonate

Base Information

Chemical Name:(1R,4S,5S)-4-((S)-1,2-bis(benzyloxy)ethyl)-5-fluorocyclopent-2-enyl methyl carbonate
CAS No.:1309594-32-8
Molecular Formula:C₂₃H₂₅FO₅
Molecular Weight:400.447
Hs Code.:

Synonyms:(1R,4S,5S)-4-((S)-1,2-bis(benzyloxy)ethyl)-5-fluorocyclopent-2-enyl methyl carbonate

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Chemical Property of (1R,4S,5S)-4-((S)-1,2-bis(benzyloxy)ethyl)-5-fluorocyclopent-2-enyl methyl carbonate

Chemical Property:

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Technology Process of (1R,4S,5S)-4-((S)-1,2-bis(benzyloxy)ethyl)-5-fluorocyclopent-2-enyl methyl carbonate

There total 8 articles about (1R,4S,5S)-4-((S)-1,2-bis(benzyloxy)ethyl)-5-fluorocyclopent-2-enyl methyl carbonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

: 1309594-29-3
(1R,4S,5S)-4-((S)-1,2-bis(benzyloxy)ethyl)-5-fluorocyclopent-2-enol

: 79-22-1
methyl chloroformate

: 1309594-32-8
(1R,4S,5S)-4-((S)-1,2-bis(benzyloxy)ethyl)-5-fluorocyclopent-2-enyl methyl carbonate

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/j.tet.2011.03.054

Reference yield:

: 1309594-25-9
(2S,3S)-3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoro-N-methoxy-N-methylpent-4-enamide

: 1309594-32-8
(1R,4S,5S)-4-((S)-1,2-bis(benzyloxy)ethyl)-5-fluorocyclopent-2-enyl methyl carbonate

Guidance literature:: Multi-step reaction with 5 steps

1: tetrahydrofuran / 1 h / -78 °C

2: triethylamine / tetrahydrofuran

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 16 h / 100 °C

4: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C

5: pyridine / dichloromethane / 1 h / 0 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium tetrahydroborate; cerium(III) chloride heptahydrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; 4: Luche reduction;
DOI:10.1016/j.tet.2011.03.054

Reference yield:

: 1309594-26-0
(5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-5-fluoroocta-2,7-dien-4-one

: 1309594-32-8
(1R,4S,5S)-4-((S)-1,2-bis(benzyloxy)ethyl)-5-fluorocyclopent-2-enyl methyl carbonate

Guidance literature:: Multi-step reaction with 3 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 16 h / 100 °C

2: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C

3: pyridine / dichloromethane / 1 h / 0 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; dichloromethane; toluene; 2: Luche reduction;
DOI:10.1016/j.tet.2011.03.054